6007-85-8

Basic information

• Product Name: THIOPHENE-3,4-DICARBOXYLIC ACID
• Synonyms: THIOPHENE-3,4-DICARBOXYLIC ACID;3,4-THIOPHENEDICARBOXYLIC ACID;1H,3H-Thieno[3,4-c]furan-1,3-dione;3,4-Thiophenedicarboxylic Anhydride;3,4-Thiophenedicarboxylic acid anhydride;NSC 241105;Thieno[3,4-c]furan-1,3-dione
• CAS NO: 6007-85-8
• Molecular Formula: C₆H₂O₃S
• Molecular Weight: 172.16
• Mol File: 6007-85-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 144.5-146.5℃ (toluene )
• Boiling Point: 306.4 °C at 760 mmHg
• Flash Point: 139.1 °C
• Appearance: /
• Density: 1.674 g/cm³
• Vapor Pressure: 0.000772mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: slightly sol. in Toluene
• CAS DataBase Reference: THIOPHENE-3,4-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: THIOPHENE-3,4-DICARBOXYLIC ACID(6007-85-8)
• EPA Substance Registry System: THIOPHENE-3,4-DICARBOXYLIC ACID(6007-85-8)

Safety Data

• Hazardous Substances Data: 6007-85-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H2O3S/c7-5-3-1-10-2-4(3)6(8)9-5/h1-2H

Synthetic route

thiophene-3,4-dicarboxylic acid (4282-29-5) → 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8)

Conditions	Yield
With acetic anhydride at 110℃;	100%
With acetic anhydride at 140℃; for 12h;	95%
With acetic anhydride	93%

thiophene-2,3,4,5-tetracarboxylic acid (4506-94-9) → 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8)

Conditions	Yield
at 220℃;

4-oxa-10-thia-tricyclo[5.2.1.02,6]deca-2(6),8-diene-3,5-dione → 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8)

Conditions	Yield
under 0.00375 Torr; Pyrolysis;

C12H8O4S → 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 370 °C / 0 Torr / Pyrolysis 2: 0 Torr / Pyrolysis View Scheme

3,4-dicyanothiophene (18853-32-2) → 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / KOH / ethane-1,2-diol / Heating 2: 86 percent / Ac2O / 140 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide / ethylene glycol / 4 h 1.2: Cooling with ice 2.1: acetic anhydride / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / ethylene glycol / 4 h / Heating / reflux 2: acetic anhydride / 3 h / Heating / reflux View Scheme

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + 6-aminoundecane (33788-00-0) → 4-[[1-pentylhexylamino]carbonyl]-3-thiophenecarboxylic acid (1332524-83-0)

Conditions	Yield
In toluene for 24h; Reflux;	98%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + n-Dodecylamine (124-22-1) → 4-dodecylcarbamoylthiophene-3-carboxylic acid (847053-25-2)

Conditions	Yield
In toluene	97%
In toluene	97%
In toluene for 24h; Heating;	93%
In toluene Reflux; Inert atmosphere;
In toluene at 110℃; for 12h; Inert atmosphere;

2-Ethylhexylamine (104-75-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (1231160-82-9)

Conditions	Yield
Stage #1: 2-Ethylhexylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 140℃; for 24h; Inert atmosphere; Stage #2: With thionyl chloride at 140℃; for 3h; Inert atmosphere;	96%
In acetic acid Inert atmosphere; Reflux; Schlenk technique;
Stage #1: 2-Ethylhexylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 140℃; for 24h; Stage #2: With thionyl chloride for 3h; Reflux;	6.20 g
Stage #1: 2-Ethylhexylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene Reflux; Stage #2: With thionyl chloride for 4h; Reflux;

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + 2-octyldodecylamine (62281-06-5) → C26H45NO3S (1287306-18-6)

Conditions	Yield
In toluene for 24h; Reflux;	95.3%
In toluene Reflux; Inert atmosphere;

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + 1-hexylheptylamine (22513-16-2) → 4-[[1-hexylheptylamino]carbonyl]-3-thiophenecarboxylic acid (1332524-74-9)

Conditions	Yield
In toluene for 24h; Reflux;	94%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + 1-aminooctadecane (124-30-1) → 4-(octadecylaminocarbonyl)-3-thiophenecarboxylic acid (1332524-59-0)

Conditions	Yield
In toluene for 24h; Reflux;	94%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + 2-octyldodecylamine (62281-06-5) → 5-(2-octyl-1-dodecyl)-4H-thieno[3,4-c]pyrrol-4,6(5H)-dione (1234271-13-6)

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; 2-octyldodecylamine In toluene for 24h; Reflux; Stage #2: With thionyl chloride for 3h; Reflux;	92%
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; 2-octyldodecylamine With dmap In 1,4-dioxane at 55℃; for 20h; Inert atmosphere; Schlenk technique; Stage #2: With acetic anhydride In 1,4-dioxane at 80℃; for 4h; Inert atmosphere; Schlenk technique;	85%
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; 2-octyldodecylamine In toluene for 24h; Reflux; Stage #2: With thionyl chloride at 75℃; for 3h;	74%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + hexan-1-amine (111-26-2) → 1,3-dibromo-5-(n-hexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (566939-56-8)

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; hexan-1-amine In toluene at 120℃; for 24h; Inert atmosphere; Stage #2: With pyridine; sulfurous dibromide In toluene at 0 - 120℃; for 29h; Inert atmosphere;	90.23%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + n-Dodecylamine (124-22-1) → 1,3-dibromo-5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (773881-47-3)

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; n-Dodecylamine In toluene at 90℃; for 15h; Inert atmosphere; Stage #2: With pyridine; sulfurous dibromide In toluene at 0 - 110℃; for 17h; Inert atmosphere;	90.18%

2-Ethylhexylamine (104-75-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (1231160-83-0)

Conditions	Yield
Stage #1: 2-Ethylhexylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 130℃; for 20h; Inert atmosphere; Stage #2: With pyridine; sulfurous dibromide In toluene at 0 - 130℃; for 23h; Reagent/catalyst; Temperature; Inert atmosphere;	90%

2-decyl-1-tetradecylamine (62281-07-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 1,3-dibromo-5-(2-decyltetradecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 120℃; for 24h; Inert atmosphere; Stage #2: With pyridine; sulfurous dibromide In toluene at 0 - 120℃; for 29h; Inert atmosphere;	89.98%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + ethylamine (75-04-7) → C8H5Br2NO2S

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; ethylamine In toluene at 120℃; for 24h; Inert atmosphere; Stage #2: With pyridine; sulfurous dibromide In toluene at 0 - 120℃; for 29h; Inert atmosphere;	89%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + (3S)-3-aminoazepan-2-one hydrochloride → (S)-5-(2-oxoazepan-3-yl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; (3S)-3-aminoazepan-2-one hydrochloride With trimethylamine In tetrahydrofuran at 20℃; for 18h; Stage #2: With 1,1'-carbonyldiimidazole In tetrahydrofuran at 64℃; for 2h;	89%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + n-Octylamine (111-86-4) → 4-octylcarbamoylthiophene-3-carboxylic acid (847052-87-3)

Conditions	Yield
In toluene for 24h; Heating;	85%
In toluene at 180℃; for 24h; Inert atmosphere;	73%
In N,N-dimethyl-formamide Inert atmosphere; Heating;
In toluene for 24h; Reflux;
In toluene for 24h; Reflux;

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + hexan-1-amine (111-26-2) → 5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (566939-54-6)

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; hexan-1-amine In toluene at 140℃; for 24h; Inert atmosphere; Stage #2: With thionyl chloride at 140℃; for 3h; Inert atmosphere;	85%
In acetic acid Inert atmosphere; Reflux; Schlenk technique;
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; hexan-1-amine In toluene at 140℃; for 24h; Stage #2: With thionyl chloride for 3h; Reflux;	5.90 g

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + n-Octylamine (111-86-4) → 5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (773881-43-9)

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; n-Octylamine In toluene at 140℃; for 24h; Inert atmosphere; Stage #2: With thionyl chloride at 140℃; for 3h; Inert atmosphere;	84%
With thionyl chloride
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; n-Octylamine In toluene at 24℃; Reflux; Stage #2: With thionyl chloride at 4℃; Reflux;	4.12 g

2-decyl-1-tetradecylamine (62281-07-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 5-(2-decyltetradecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
Stage #1: 2-decyl-1-tetradecylamine; 1H,3H-thieno[3,4-c]furan-1,3-dione In toluene at 100℃; for 24h; Stage #2: With thionyl chloride at 80℃; for 4h;	74%
With thionyl chloride In toluene

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + 5-decylheptadecan-1-amine (1370523-47-9) → 5-(5-decylheptadecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
With thionyl chloride In toluene at 100℃; for 24h; Gabriel Amine Synthesis;	73%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + 5-hexyltridecan-1-amine → 5-(5-hexyltridecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
In toluene at 100℃; for 24h;	73%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + ethyl acetoacetate (141-97-9) → 4H-cyclopenta[c]thiophene-4,6(5H)dione (246232-39-3)

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; ethyl acetoacetate With acetic anhydride; triethylamine at 65℃; Claisen Condensation; Stage #2: With hydrogenchloride In water for 0.166667h; Claisen Condensation; Reflux;	71%
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; ethyl acetoacetate With triethylamine In acetic anhydride at 65℃; Inert atmosphere; Stage #2: With hydrogenchloride In water at 70℃; for 0.166667h;	906.6 mg

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + benzene (71-43-2) → 3-benzoylthiophene-4-carboxylic acid (30011-77-9)

Conditions	Yield
With aluminum (III) chloride at 20℃; for 5h;	70%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 2-nitrothiophene-3,4-dicarboxylic acid (932032-15-0)

Conditions	Yield
With nitric acid at 0 - 20℃; for 2h;	66%
With nitric acid at 0 - 5℃; for 0.5h;
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione With nitric acid at 0 - 5℃; for 0.5h; Stage #2: With water

fluorobenzene (462-06-6) + 1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 4-(4-fluorobenzoyl)thiophene-3-carboxylic acid (168542-28-7)

Conditions	Yield
With aluminium trichloride for 3.5h; Heating;	65%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + cyclohexylamine (108-91-8) → 5-cyclohexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; cyclohexylamine In toluene at 140℃; for 24h; Inert atmosphere; Stage #2: With thionyl chloride at 140℃; for 3h; Inert atmosphere;	65%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + 3,3'-(dimethylsilanediyl)bis(4-bromo-N,N-dimethylaniline) → C24H26N2O2SSi

Conditions	Yield
Stage #1: 3,3'-(dimethylsilanediyl)bis(4-bromo-N,N-dimethylaniline) With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: With lanthanium (III) chloride bis(lithium chloride) complex In tetrahydrofuran; pentane at -78℃; for 0.5h; Stage #3: 1H,3H-thieno[3,4-c]furan-1,3-dione In tetrahydrofuran; pentane at -78 - 20℃;	57%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + n-Dodecylamine (124-22-1) → 5-dodecyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione (773881-44-0)

Conditions	Yield
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; n-Dodecylamine In toluene for 24h; Reflux; Stage #2: With thionyl chloride for 6h; Reflux;	55%
Stage #1: 1H,3H-thieno[3,4-c]furan-1,3-dione; n-Dodecylamine In toluene for 24h; Reflux; Stage #2: With thionyl chloride for 5h; Reflux;	50.5%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) + anthracene (120-12-7) → 2-Thia-cyclopenta[b]naphthacene-4,13-dione (78076-69-4) + 2-Thia-indeno[5,6-a]anthracene-4,13-dione (78076-70-7)

Conditions	Yield
at 315℃; for 0.2h;	A 1.8% B 1.6%

1H,3H-thieno[3,4-c]furan-1,3-dione (6007-85-8) → 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0) + 4,8-Dihydrobenzo<1,2-b:4,5-c'>dithiophen-4,8-dion (33527-22-9)

Conditions	Yield
at 470℃; for 0.00833333h;	A 0.12% B 0.36%

Upstream product

• 60078-54-8 1H-Benzimidazol-2-amine,1-(2-chloroethyl)-(9CI) 
• 60078-53-7 1H-Benzimidazole-1-ethanol,2-(methylamino)-(9CI) 
• 6007-83-6 thieno[2,3-c]furan-4,6-dione 
• 60078-16-2 5-oxo-3-phenyl-2,5-dihydro-1,2,3,4-thiatriazol-3-ium 
• 60078-11-7 3-phenyl-5-thioxo-2,5-dihydro-1,2,3,4-oxatriazol-3-ium 
• 6007-78-9 alpha-oxothiophen-2-acetonitrile 
• 6007-77-8 4-(2,5-DIMETHYLTHIEN-3-YL)-4-OXOBUTANOIC ACID 
• 60077-68-1 (2R,5S)-6β-Hydroxymethyl-10β-methyl-2-(1-methylvinyl)spiro[4.5]decan-8-one 
• 60077-63-6 (2R)-1,2,12,12aα-Tetrahydro-5,6aα-dihydroxy-8,9-dimethoxy-2α-(1-methylvinyl)[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one 
• 60077-62-5 villosol 
• 60077-57-8 5-Benzofurancarboxylic acid, 4-hydroxy-, methyl ester 
• 60077-56-7 (5β,7β)-11,12,13,14-Tetradehydro-14-benzylmatridin-15-one 
• 60077-55-6 (-)-7-[[3-Hydroxy-5-(6-hydroxy-2,2,6-trimethyl-3-oxocyclohexyl)-3-methylpentyl]oxy]-2H-1-benzopyran-2-one 
• 60077-54-5 (+)-7-[[5-(3,6-Dihydroxy-2,2,6-trimethylcyclohexyl)-3-hydroxy-3-methylpentyl]oxy]-2H-1-benzopyran-2-one 

Downstream Products

• 60078-77-5 1H-Benzimidazole-1-ethanamine,2-amino-(9CI) 
• 60078-92-4 3-hydroxy-2,6,6-trimethylcyclohex-1-ene-1-carbaldehyde 
• 60078-97-9 4,5-dihydro-1-phenyl-3-(2,4,6-trimethylphenyl)-1H-pyrazole 
• 6007-90-5 3-(2-Thienyl)-1-propylamine 
• 60079-22-3 2-[(3-aMino-3-carboxy-propanoyl)aMino]butane 
• 60079-51-8 H-PHG-NH2 HCL 
• 60079-77-8 methyl 2-bromo-2-(4-bromophenyl)acetate 
• 6008-01-1 N-(1-methylpropyl)-N-[2-oxo-2-(1,3-thiazol-2-ylamino)ethyl]-1,3-benzodioxole-5-carboxamide 
• 60080-38-8 doxycycline 
• 60080-69-5 methyl L-ornithine monohydrochloride 
• 60080-91-3 N-[3-(diethylamino)propyl]-2-hydroxy-N-methyl-2,2-diphenylacetamide 
• 60080-98-0 2-BROMO-5-METHOXYBENZOPHENONE 
• 60080-99-1 (2-broMo-5-Methoxyphenyl)(phenyl)Methanol 
• 600-81-7 4-Pregnen-7beta-ol-3,20-dione 

Recommend Products

• 773881-43-9  5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 
• 111-86-4  n-Octylamine 
• 108-91-8  cyclohexylamine